Acetyl chloride → HCID 90408610, compound

HRID 516575Notes

Reaction equation

HRID 516575 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([Br:18])=[CH:13][C:12]=2[F:19])[N:8]=[C:7]([C:20]([O:22][CH3:23])=[O:21])[C:6]=1[Cl:24])(=O)C.C(Cl)(=O)C.C([O-])(O)=O.[Na+]>CO.C1COCC1>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([Br:18])=[CH:13][C:12]=2[F:19])[N:8]=[C:7]([C:20]([O:22][CH3:23])=[O:21])[C:6]=1[Cl:24]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 90409643HCID 90409643, compound

Product 1

HCID 90408610HCID 90408610, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 4-acetamido-6-(4-bromo-2,5-difluorophenyl)-3-chloropicolinate (0.300 g, 0.715 mmol) in a mixture of MeOH (3.57 mL) and THF (3.57 mL) was slowly added acetyl chloride (1.017 mL, 14.30 mmol). The reaction mixture was stirred at 20° C. for 2 h. The mixture was then poured into a saturated aqueous solution of NaHCO3 and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, concentrated and dried in vacuo to afford methyl 4-amino-6-(4-bromo-2,5-difluorophenyl)-3-chloropicolinate (0.257 g, 0.681 mmol, 95%) as a white solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c841b973e1a74b38bbcc7f026d53dda0
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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